


The misadventures of Crowley and Squirrell

by Ill_write_it



Category: Supernatural
Genre: I'm so so sorry, M/M
Language: English
Status: Completed
Published: 2016-09-24
Updated: 2016-09-24
Packaged: 2018-08-17 00:51:45
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 4,399
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8124250
Author URL: https://archiveofourown.org/users/Ill_write_it/pseuds/Ill_write_it
Summary: I don't even. So ashamed I wrote this. *hides under rock*





	

“Call it off, Crowley.” Dean said gruffly. Slamming his fist onto the table. Sam glanced at him, nervously.   
“Because?” , Dean could practically hear Crowley's wolfish grin. He sighed. “Because it’s over, you son of a bitch. We want to deal.” Sam looked at him questioningly, eyeing the phone with unease. Dean's face was set in a firm grimace.   
“30 seconds.” Crowley swirled his drink on the other end of the line, the boys could hear the ice clinking against the sides of the glass.   
“We stop the trials, and you stop the killing.” Dean offered.   
“I want the Demon Tablet. The whole demon tablet.” He said.   
“Fine.” Dean replied begrudgingly. “But the Angel Tablet comes to us.”  
“On what grounds?”, Crowley sounded a little annoyed. His voice an octave higher.   
“On the grounds that you’re a douche bag.”   
“Say that to my face, Squirrel.” Crowley said, no longer crackling on the phone. He hung up. Smiling arrogantly and admiring Dean’s ass from behind. Dean’s forearm was resting on the table, all of his weight in his left leg. He spun around shocked by Crowley’s sudden appearance but trying to appear unfazed.  
“You’re a douche bag, Crowley, and no douche bag should have that much power.” he said confidently. Sam looked a little startled, his mouth hanging slightly open.   
“Don’t be so surprised Moose, it’s not hard to trace a phone call.” The Demon waggled the phone in his hand triumphantly. Sam shut his mouth, embarrassed. Then turned to look at Dean.   
“But, I thought - “ Sam started but Dean cut him off with a warning glance, heaven forbid Crowley find out anything else about the Men Of Letters Bunker.  
Crowley huffed expectantly, looking at Dean; but when Dean didn’t speak, Crowley sighed. “You can have your deal,” Crowley’s smile had faded. “But first.” He raised the hand holding his glass of Craig, grinning once again; “I need to hear two… little words.” he swirled the alcohol and moved closer to Dean. “Tell me you surrender, Dean, and we have an agreement.”   
Dean rolled his eyes and looked across to Sam, who was sitting at the table with his unchanging confused expression.   
“Well?”   
Dean said nothing, his eyes downcast.   
“I guess I’ll just have to make you.” Crowley smiled placing his free hand on Deans shoulder, having placed his phone back into his pocket. They disappeared leaving Sam lost for words at the table, desperately worried for both Dean's, and Crowley’s next victims safety.   
*********  
“What the - Where the hell am I? “ Dean struggled. His hands and feet were bound to the wooden chair frame, leaving him in a rather vulnerable position. “Crowley! Where the hell am I?” He growled.   
“Close but no cigar.” Crowley said, gesturing with his index finger and grinning. When Dean broke free of his chains he was going to wipe that smug little smile off of his face. “An, apartment of mine. I keep it for… special occasions.” Crowley said circling Dean. Dean’s eyes were just becoming adjusted as he took in the lavish room. Marble flooring with a rug that had been moved out of the way for his current seating arrangement. And when he stretched his neck, he could just about make out a bed behind him. Crowley watched him drink in his surroundings.   
“When Sam gets here -“ Dean started.   
“Sam won’t find you for a little while yet. And I promise, once you’ve said what you need to say; you’ll be home in no time.”  
“I’ve been to hell, Crowley. I’ve been to friggin’ purgatory.” Dean raised his voice, straining against his bonds. “And there is no form of torture I have not endured. What could you possibly do to me, that hasn’t been done already.”  
Crowley feigned a hurt expression, pressing his free hand to his chest. “You insult me, Winchester. I am very...” He walked towards Dean, positioning himself between Deans open legs and traced his free hand over Deans cheek. Dean turned his face away. “Creative.” Crowley finished. He walked away from Dean and placed his Craig on the surface of the maplewood dresser, he proceeded to remove his jacket and roll up his sleeves. Dean was sweating and , although he would never admit it, it wasn’t because the room was overly warm- he was terrified. He wondered what Sam was thinking, if Crowley’s planned victim was even still breathing. He inhaled shakily, desperately searching for some confidence deep inside to maintain his cocky exterior.   
Crowley sauntered back over to him. “The thing that I like most about you, Squirrel,” He placed his hand firmly under Deans jaw, holding his head up so he could look him straight in the eye. “Is that, pain, doesn’t scare you. Does it?” Dean struggled against his hand, but to no avail. Crowley made his puppet shake his head violently. “No My handsome King” Crowley impersonated in a comedic voice. Dean’s hatred was written all across his beautiful features. The Demon continued; “But the beauty of it is, that I don’t have to hurt you to make you surrender.” he released his hand and Dean ground his teeth. “In fact, I have to do the complete opposite.” Crowley adjusted his sleeves before returning to Dean and gently tracing his index finger along Deans cheekbone. Dean tried to turn away, “No Squirrel, don’t run from me.” The king growled. “Let me go Crowley.” Dean’s mouth was dry, he licked his lips . Crowley locked eyes with Dean and rested both his hands on Dean’s shoulders, Dean looked frightened. “Don’t be frightened Squirrel.” he said, bringing his face closer and closer to Dean’s, kissing distance. Dean tried to turn away, but an invisible force was holding his head in place; and he wasn’t entirely sure it was Crowley’s doing.”When I get free,” Dean said slowly. “I’m going to tear you to shreds.” he spat.  
“If, you get free.” Crowley whispered, wiping the spit off his face with a red silk handkerchief. “When you surrender.” He licked his lips. Dean glanced down at them. Shaking like a leaf, he copied the action. He felt Crowley’s scotch laced breath, warm on his face, as Crowley came close again. It gave him goosebumps and Crowley noticed. Dean felt a warm hand at the back of his head, holding his face tilted up towards Crowley. Dean closed his eyes, waiting for the sweet taste of the barbaric Demon on his soft pink lips, wondering if the taste of sulphur would be overwhelming or if it was well masked by the vast quantities of alcohol... But nothing happened.   
“It seems to be working quite well.” Crowley mused, tracing a hand lazily down Dean’s leg, and leaning away to look over Dean’s body, he leaned in again and whispered. “You feel tense, sweetheart.” Glancing briefly at Dean’s crotch.  
“Screw you.” he said breathlessly   
“Oh, I assure you the only one of us getting screwed here.” Crowley walked around Dean, drinking in the beauty of this marvellous creature and when he was behind the handsome hunter, he placed his hands on his shoulders and his head alongside Dean's. "Will be you.” Crowley growled into Dean’s ear, nipping on his left earlobe for clarity. Dean gasped, the demon chuckled in response.   
“Get off of me.” Dean whimpered, pleading with the demon who was circling him again, stopping when he was directly in front of his captive, admiring Dean’s obvious arousal.   
“I don’t think you want that, do you squirrel?” Dean threw his head back as Crowley palmed his erection. “Hmm?”   
“Fuck.” Dean whimpered.   
“Thought not.” Crowley mused. stroking the seam of Dean’s jeans tauntingly.   
“Now then Squirrel.” He said, eyes fixed on Dean’s groin. “Isn’t there something you wanted to say?” he waited, the silence deafening.   
“Go. To. Hell.” Dean choked out.   
“Wrong answer” Crowley growled as he increased the pressure of his strokes. “Say it, and I’ll give you what you desire.”   
“And what is it that I desire?” feigning nonchalance, Dean tried not to moan as Crowley clicked his fingers, removing Dean’s shirt and jeans, everything was colder and that only heightened any sensations. A light breeze from an open window aggravated his barely recovering goosebumps. At least this time he had an excuse.   
“Why don’t you show me? Hmm.” Crowley said, playfully as he undid Dean’s bonds, knowing full well that Dean wasn’t going to get anywhere, no matter how hard he tried: Crowley was a demon after all.   
Once Dean was free he violently launched himself at the king of hell, wrapping his strong - albeit, unclothed - arms around Crowley's torso in an desperate effort to throw him to the ground and escape. Crowley didn’t move. He just looked down at Dean, with an amused and rather smug smile taking over his features. “Sorry, Squirrel, I’m not moving.” he said, his hand finding its way into Dean’s hair to tilt his face up towards the demon, so he could watch that innocent little frightened expression. “But while you’re down there.” Crowley smiled again.   
“Crowley.” Dean’s voice warned, trying to pull his head away. His knees had slipped under him. He was kneeling before the king of hell. With his face, just a little too close to…   
“King.” Crowley commanded, his voice booming. Dean looked away, his eyes downcast as Crowley held a firm grip on his head. “Look at me.” Crowley demanded, pulling him back. But when Dean refused to change the focus of his emerald green eyes, Crowley repeated his instruction. “Look at me, Winchester.” he said, anger seeping through his supposedly calm facade. Dean reluctantly looked up, the red rush from rebellious disobedience clear in his features.   
“Such a pretty boy.” Crowley mumbled, his thumb rubbing small circles in Dean’s hair. He crouched down to Dean’s level and wrapped his hands around Dean’s head, elbows adjacent to Dean’s shoulders. Dean was still kneeling, but Crowley lowering himself allowed Dean to drop down so his weight was resting on his heels with his feet tucked neatly behind him. “Why don’t you just make this easier for yourself, and do as you're told. Then you can,” Crowley paused to look into Dean’s green eyes and run his left hand through the hunters hair. “you can have your reward. Wouldn’t that be good. Hmm?” Dean’s lips were pursed defiantly. “Just give me your submission.” Crowley continued to whisper, shuffling closer, his fingers winding into Dean’s blondish hair. Crowley waited for a response. Dean seemed to be almost weighing up his options. Crowley searched his face for any indication of his choice.   
“Go to Hell.” Dean spat, his lips pressed firmly together.   
“That is no way to address your king.” Crowley wasn’t angry, just a little disappointed. But also excited by the prospect of punishing Dean for his defiant actions. He stood. Straightening out his creased suit trousers, then he pulled Dean to his feet and placed him firmly back onto the chair. Dean tried to fight him, but Crowley’s demonic powers weren’t allowing him to do anything other than move his head. Crowley began to stroke him again through the thin fabric of his boxers, mumbling to himself about how “It would be so much easier.” and “You’d enjoy it Squirrel.” Dean had given up trying to hide his erection, without the fabric of his jeans it was practically impossible. It was infuriating, Crowley continued without changing pace, or direction for minutes and minutes getting Dean closer and closer but never letting him climax. After ten or so minutes, Dean was close to begging; but he was Dean Winchester, and he would not be Crowley’s bitch. When Crowley stopped, Dean had intended to sigh with boredom, tell the bastard how shit he was at this. But Crowley didn’t stop, he seemed to have endless amounts of patience. Dean threw his head back and tried to buck his hips up into the movement to find some more friction, not expecting to be able to move at all. He was pleasantly surprised. “Naughty Squirrel.” Crowley tutted. Tightening his grip. Dean was so shocked he couldn’t stop the moan from escaping. Embarrassed, he blushed. “Shut up Crowley, if you’re not going to… If you’re. Just unbind me and..” Dean groaned. How did he put this.   
“I told you Squirrel, all I need are those two little words.” Crowley said. Increasing his pressure again.   
“No ~” Dean said, the change in Crowley's dynamic making him sound like a twink whose voice was cracking.   
“No?” Crowley questioned, speeding and slowing with no regard to Dean’s cries.   
“Please Crowley.” Dean wasn’t begging, he wasn’t.   
“Excuse me.” Crowley stopped. Dean tried to move again, but he couldn’t. Crowley returned his focus to Dean’s eyes. “What did you call me?”   
“Crow - “ Crowley fastened his hands around Dean’s throat.   
“Haven’t we already addressed this problem, Dean?" He released his grip and Dean regained his breath. "Do you not understand why I am punishing you? Maybe this isn’t enough of a punishment. What do you think?” Dean whined unhappily, unable to make his usual manly sounds at his current overwhelmingly sensual state of arousal. Already reduced to pleading at the feet of the king of hell.  
"Beg me again , Winchester." Crowley said. His hands resting at his sides.   
"Screw you " Crowley cut him off with a sharp slap to his right cheek. "Try again." Dean dropped his head to the ground. Crowley inhaled loudly. "Fine, have it your way, Squirrel." Dean was frightened, Crowley was unpredictable. When would Sam get here?   
Crowley pulled him off the chair, Dean found he could move his limbs again and tried to stand. A palm on his forehead kept him on the ground, accomplanied by a sharp "No," through gritted teeth. Dean stayed where Crowley had placed him. Crossing his legs and watching Crowley move across the room, Dean was smirking, dressing himself back up with confidence to feel safer in the hands of this madman. When would Sammy get here?  
Crowley made his way to the bed, Dean's smile shrinking, unlike his pestering erection. He sat on the edge of the bed. "Come here squirrel," He smiled , patting his lap. Dean raised his eyebrows. Crowley returned his expression. "Come here now and I'll go easy on you."  
"Damn it," Dean cursed under his breath. And went to stand.   
"No." Crowley used his power to push him back onto his knees. Dean tried agian. "I said, no." Crowley sighed. "Crawl, pet. Crawl to me and recieve your punishment."   
"I'm not a -" Dean started.  
"Patience is not one of my virtues, not that I have virtues, but if I did. Then when it comes to disobedience. Patience is not one of them. You should know that by now Squirrel. Now, " Before Crowley could say 'crawl' Dean was making his way across the room, failing to maintain his dignity. He looked so perfect like that. Crawling towards his master. Perfect, Crowley thought.   
"Damn it." Dean cursed again, avoiding Crowley's gaze as he reached his feet.   
"I heard that." The Demon scolded. He placed his hands firmly under Dean's arms and pulled him up. "Now, lay across my knees."   
"What!" Dean replied, stunned.   
"You heard me." he responded disapporiving of Dean's current stature. Why did the man have to be so darn tall?   
Dean crossed his arms, but before he could say 'no' Crowley had him defenseless, splayed across his woollen suit trousers, Crowley placed his hand firmly on the small of Dean's back. "Now," Dean could hear him smiling as a knot of fear and arousal grew in the base of his abdomen.. and lower. Crowley chuckled. Dean swallowed, desperatly embarrased; having lost all hope of regaining his dignity, he relaxed a little, pressing his face into Crowley's leg and praying this would all be over soon. "Good Squirrel." Crowley praised him, patting him softly on his ass. Dean winced. Wishing Sam would hurry up already.  
"How many strikes does Squirrel get?" Crowley was tracing patterns on Dean's back. He felt exposed, trying desperately not to hunch around Crowley's legs.   
"What do you think, Squirrel?" he turned his head, miming listening to Dean, waiting for a sarcastic reply.   
"Howabout, Squirrel gets some pie and a ticket home." Dean compained, he didn't get a verbal response. just the sound and sensation of Crowley's hand coming down hard on his left buttock. He jerked in surprise. Tensing for the next strike, Dean waited; but it didn't come. Then, out of the blue, another. It stung. Dean had been beaten, tortured, stabbed, shot, broken and had felt every form of pain known to man. But this, this was so controlled so... Crowley spanked him again... considered. After several perfectly timed 'strikes' Dean was feeling it, but not where he expected. Although his ass stung and with each strike he was sure he had bruises, it was nothing compared to his aching hard-on brushing against Crowley's leg. He wanted, he needed to touch himself so badly. "Do you think that's enough Squirrel?" Dean turned his head to look at Crowley, his tone was condescending, but Dean was no longer fighting him.   
"Hmm?" Crowley asked. "Evidently not.." He raised his hand.  
"No wait, please." Dean said quietly.   
Crowley tilted his head, gesturing with his hand in a circular motion, as if he wanted Dean to continue.   
"I've learn't my lesson" Dean dipped his head in shame.   
"Evidently you have not," Crowley emphasised his statement with another slap to Dean's posterior. Dean groaned involuntarily as his unbearable erection brushed tantalizingly against Crowley.  
"I've learn't my lesson." Dean inhaled. "sir."   
"That's much better," Crowley praised and Dean winced as crowley patted him twice gently on the butt. "Wasn't difficult, was it Squirrel?" Dean sighed. Crowley traced his hand over Dean's back again. Drawing patterns in his flesh visible to no one but the king himself. Dean moved himself, shuffling around; still lying across Crowley's knee. "Something troubling you Squirrel?" He questioned, grinning.   
"You know -" Dean began angrily, "Yes, Sir." he corrected himself begrudginly.   
"And what might that be?" Crowley asked.   
"If you don't mind. I'd like to, be able to, ah.. Um. Move... Sir." Dean said. Blushing.  
"And why would you want to move? Are you uncomfortable love?" Crowley mused innocently, although his expression showed his true understanding of Dean's plausible motives was far from innocent.   
Dean didn't reply: too embarrassed to voice his needs. Crowley tried to prompt him by moving his knee to brush against Dean's cock, all this earned him was a growl. "You've been such a good squirrel, I think squirrel deserves a reward."   
"Can I go back now?" Dean questioned hopefully.   
"So modest Dean!" Crowley remarked. "I'm sure I can help you with your little problem, if you'd let me?" Crowley stroked his sore ass. "Would you like that?"   
Dean didn't reply, only buried his head into Crowley's leg. "Hmm?" Crowley prompted.  
"Yes," Dean admitted barely audible.   
"That's not quite convincing enough, try a little"," Crowley shifted again and Dean moaned "try a little.. Harder."   
"Please touch me sir." Dean said.  
"Much better." Crowley pulled Dean off his knees and laid him down across the bed with his head resting against the pillows and his legs draped over Crowley's own. "Don't be shy squirrel." He pulled down Dean's damp boxers freeing his dick. Dean grunted, his eyes closed. "Look at me, Dean. I want you to look at me while I make you come again and again and again." Crowley grasped Dean's dick, jerking him off; giving him all the pleasure he had denied him earlier. Dean bucked into the movement, writhing beneath Crowley's touch. Desperate for more. "Stay still." Crowley grunted. Dean couldn't hear him as waves of pleasure consumed him. "I said, still, squirrel" he warned. "Do I have to restrain you again?" Dean desperately tried to control himself "no" he said breathlessly .   
"Pardon?" Crowley said. Dean had his eyes closed and his head thrown back in ecstasy. Crowley stopped. Dean whimpered with the loss of the pleasure. Crowley made his way up the bed to Dean, his face hovering over Dean's. Dean felt the closeness of Crowley and opened his eyes. "I don't think you quite understand." Crowley growled, his hands looped in Dean's hair, shins trapping Dean's thighs. "You're my bitch, Winchester."   
Dean clenched his jaw, realising what he had just succumbed to, he tried to move away from Crowley.   
"You're the bottom in this relationship."  
"Screw you Crowley. You've had your kicks. Your twisted little kinks. Let me go, bastard."  
"Not until you have learnt your place." He flipped Dean and pulled his ass into the air. " and just to clarify," he breathed into Dean's ear. " your place is beneath me."   
Dean couldn't speak, he didn't know what to say. He felt so ashamed he had let Crowley touch him, fondle him and bring him to climax again and again,he had called him 'sir'. Then he felt it, a finger running along his crack, teasing him open,   
"Suck." Crowley instructed, another finger pressed against his lips. Dean didn't open his mouth. "This so the only lubrication you're getting, so unless you want to really startle moose when you're incapable of walking, I suggest you do as you're told." Dean was frozen. "Alright then." Crowley shifted, preparing to the remove his finger from Dean's lips. Dean reacted quickly, taking the finger into his mouth, sucking and licking for all he was worth. "Are you sure this is your first time" Crowley's weight was pushed against him, Dean could feel his boner through the cloth of his trousers,and God was he huge.  
"Having a good time with kitten are you?" Crowley chuckled. "Can't blame you, he has - what you call - sex appeal."   
"No, Cas and I... Just no." Dean said as Crowley removed his spit coated fingers. "Perfect, " his velvet voice replied. "You'll be nice and tight for your King."  
Dean couldn't help but snigger, it earned him a hard slap to his rear. "Silence squirrel," Crowley growled menacingly.   
Crowley firmly inserted his index finger into Dean, who was trying hard not to acknowledge the intense pain, and immense pleasure he was feeling. He wouldn't give Crowley the satisfaction. Crowley was gentle, pumping his finger into Dean. Dean was enjoying it, although he'd never admit it; he was enjoying being the fuck toy of the king of hell.   
Crowley added a second finger, the surprise elicited a sharp moan from Dean.  
"Good boy." Crowley said gently. After a little while Crowley began to slow his pace, preparing to add a third finger, what he wasn't expecting was Dean to respond by moving himself onto Crowley's fingers. "Enjoying yourself, squirrel." He asked to no one in particular. Dean responded by moaning... Loudly. Crowley scissored his fingers in and out of Dean. "As much as I hate you squirrel, I'd hate to hurt your perfect little ass, so we have to go slowly."   
"Please, I need more" Dean whimpered.  
He was so perfect like this, ass pointed to Crowley, moaning and begging for more. Crowley responded to his request by adding a third and final finger. "You're such a good boy." He coaxed Dean. Gently stroking the small of his back. When Crowley was satisfied that Dean was ready, he removed the fingers. Dean whined like a bitch in heat and swivelled around. "Now now squirrel, don't make me.." But Crowley was taken back by Dean's actions. "My, my" he gawked as Dean unbuckled his belt, and struggled to undo his fly. "Why is this so difficult." Dean complained, looking up hopefully at Crowley.  
"I'm not going to help. You want me to fuck you, you've got to work for it squirrel." He chuckled.  
Dean ripped his trousers apart.  
"Hey! Those were expensive." Crowley objected. Dean pulled down his pants and underwear and swallowed loudly. "Don't be scared squirrel, you're all nice and prepared." Dean looked up expectantly. Crowley rolled his eyes and tossed Dean back onto his front. "So eager." He said pushing a finger into Dean's ass, Dean pushed himself back against Crowley. "Tell me what you want squirrel, tell me what it is that you need."   
Dean moaned.  
"Not quite graphic enough." Crowley complained.   
"I want you to fill me, sir"  
"Good Squirrel." Crowley praised. Lining himself up with Dean's entrance. He went slowly, with a cock so big he knew Dean was going to hurt. But Dean took it well, silent and waiting. And when Crowley was half way in. Dean gave up with patience and impaled himself on Crowley with a grunt. Crowley moaned in surprise. "So good for me squirrel, such a good boy for your King." Crowley gently stroked Dean's back.  
"Fuck me already." Dean whined.  
" so needy." Crowley complimented. Moving slowly in and out of Dean. "So vocal" Dean's moans were so hot. So heavy with lust. Crowley thrust into Dean gently at first, but soon set a punishing rhythm, his balls slapping Dean in time with Dean's cries of pain and pleasure. Whenever Crowley thought Dean was close he would slow, almost to a stop and whisper "not yet" after the fifth time he had done this tears were silently dripping down Dean's face. He was begging. "Please" he whimpered.   
"What would you like squirrel? I want to hear you say it"  
"Please let me come sir."   
"You'll have to try a little harder then that, Crowley changed his angle, hitting Dean's prostate hard and then moving away. Dean cried out.   
"Please my King, please let me come, I'm begging you. Please."  
"Not good enough." Crowley replied sending shivers down Dean's exhausted spine.  
"I surrender." Crowley hit him hard and fast, repeatedly striking his prostate.   
"You have permission." They came together, Crowley riding him through his orgasm, Dean fell off the edge into oblivion, he almost blacked out. Crowley wrapped his arms around his exhausted hunter. Pulling him into his lap. Dean draped himself over Crowley. Breathing softy. They sat like this, wrapped in one another and sharing the orgasmic glow. Until Dean said; "with my surrender..."   
"Yes Dean?" Crowley asked.  
"I have one condition." He nuzzled into Crowley's neck. Crowley pulled his shoulders back to look into his beautiful green eyes.   
"What's that?"   
"..." Dean looked a little sheepish.   
"The condition is that, um...." Crowley silenced home with a gentle kiss.   
"Am I correct?" He asked when they broke apart.   
Dean sighed contentedly and nodded. Kissing Crowley again. "I surrender."


End file.
